Microbicidal agents on the basis of biphenylbenzamide derivatives

ABSTRACT

The present invention relates to novel microbicidal compositions based on biphenylbenzamide derivatives of the formula (I) 
                         
in which R 1 , R 2 , R 3  and m are as defined in the disclosure, to novel biphenylbenzamides, to a plurality of processes for preparing these substances and their use for controlling pests, and to novel intermediates and processes for their preparation.

The present patent application has been filed under 35 U.S.C. 371 as anational stage application of PCT/EP03/01322, filed Feb. 11, 2003, whichwas published in German as International Patent Publication WO 03/069995on Aug. 28, 2003, and is entitled to the right of priority of GermanPatent Applications 102 07 773.8, filed Feb. 23, 2002, and 102 15 291.8,filed Apr. 8, 2002.

The present invention relates to novel microbicidal compositions basedon biphenylbenzamide derivatives, some of which are known, and to theuse of these substances for controlling unwanted microorganisms.Moreover, the invention also relates to novel biphenylbenzamidederivatives and to a plurality of processes for their preparation.

It is already known that biphenylbenzamide derivatives can be employedfor controlling species of the phytopathogenic fungus Botrytis (cf. EP-A0 545 099). However, the activity of these prior-art compounds is, inparticular at low application rates, not in all areas of use entirelysatisfactory.

Furthermore, certain biphenylbenzamide derivatives such as, for example,the compoundsN-(2′-fluoro-1,1′-biphenyl-2-yl)-2-(trifluoromethyl)benzamide andN-(4′-fluoro-1,1′-biphenyl-2-yl)-2-(trifluoromethyl)benzamide (cf. EP-A0 545 099) are known.

Hitherto, nothing has been disclosed about whether these compounds aresuitable for broad fungicidal use. Furthermore, it is not known to whatextent these compounds can be used against other microbial, for examplebacterial, pests.

It has now been found that the biphenylbenzamide derivatives, some ofwhich are known, of the formula (I)

in which

-   R¹ represents methyl, trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³ represents halogen, cyano, nitro, C₁–C₆-alkyl, C₁–C₄-alkoxy,    C₁–C₄-alkylthio, C₁–C₄-alkylsulphonyl, C₂–C₆-alkenyl,    C₃–C₆-cycloalkyl, or represents C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy,    C₁–C₆-haloalkylthio or C₁–C₆-haloalkylsulphonyl having in each case    1 to 13 halogen atoms,-   m represents 1, 2, 3, 4 or 5, where the radicals R³ may be identical    or different if m represents 2, 3, 4 or 5,    are highly suitable for controlling phytopathogenic pathogens from    the class of the Chytridiomycetes (subdivision of the    Mastigomycotina), the class of the Zygomycetes (Zygomycotina), the    class of the Hemiascomycetes, Plectomycetes, Pyrenomycetes,    Laboulbeniomycetes, Locoloascomycetes (Ascomycotina), and from the    subdivisions of the Basidiomycotina and the Deuteromycotina, and    also harmful microorganisms in the protection of materials.

Depending on the nature of the substituents, the compounds of theformula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying compositions. The invention relates both tothe use of the pure isomers and to that of the isomer mixture.

The formula (I) provides a general definition of the biphenylbenzamidederivatives which can be used according to the invention.

Preference is given to using biphenylbenzamide derivatives of theformula (I), in which

-   R¹ represents trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³ represents halogen, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio,    C₂–C₄-alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or    represents-   C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or C₁–C₄-haloalkylthio having in    each case 1 to 9 halogen atoms,-   m represents 1, 2, 3, where the radicals R³ may be identical or    different if m represents 2 or 3.

Particular preference is given to using biphenylbenzamide derivatives ofthe formula (I), in which

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,    n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, or represents C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or    C₁–C₂-haloalkylthio having in each case 1 to 5 halogen atoms,-   m represents 1, 2, where the radicals R³ may be identical or    different if m represents 2.

Very particular preference is given to using biphenylbenzamidederivatives of the formula (I), in which

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³ represents fluorine, chlorine, bromine, methyl, methoxy,    methylthio, trifluoromethyl, trifluoromethoxy or    trifluoromethylthio,-   m represents 1, 2, where the radicals R³ may be identical or    different if m represents 2.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R¹ represents trifluoromethyl.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R¹ represents iodine.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R² represents hydrogen.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R² represents fluorine.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R³ represents fluorine, chlorine or bromine.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which R³ represents trifluoromethyl,trifluoromethoxy or trifluoromethylthio.

Very particular preference is furthermore given to using compounds ofthe formula (I), in which m represents 2.

The biphenylbenzarnide derivatives of the formula (I) which can be usedaccording to the invention are highly suitable for controllingphytopathogenic pathogens of the classes Chytridiomycetes, Zygomycetes,Hemiascomycetes, Plectomycetes, Pyrenomycetes, Laboulbeniomycetes,Locoloascomycetes, Basidiomycetes and Deuteromycetes, and harmfulmicroorganisms in the protection of materials, such as Pseudomonadaceae,Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae andStreptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned by way of example, butnot by way of limitation

-   Xanthomonas species, such as, for example, Xanthomonas campestris    pv. oryzae;-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae;-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

Preferably, the compounds of the formula (I) can be used according tothe invention to control the following pathogens causing fungal andbacterial diseases:

-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae;-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

Particularly preferably, the compounds of the formula (I) can be usedaccording to the invention to control the following pathogens causingfungal and bacterial diseases:

-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae.

Some of the biphenylbenzamide derivatives of the formula (I) which canbe used according to the invention are known (cf. EP-A 0 545 099).

The biphenylbenzamide derivatives of the formula (Ia) (group 1)

in which

-   R¹ represents methyl, trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³ represents halogen, cyano, nitro, C₁–C₆-alkyl, C₁–C₄-alkoxy,    C₁–C₄-alkylthio, C₁–C₄-alkylsulphonyl, C₂–C₆-alkenyl,    C₃–C₆-cycloalkyl, or represents C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy,    C₁–C₆-haloalkylthio or C₁–C₆-haloalkylsulphonyl having in each case    1 to 13 halogen atoms,-   n represents 2, 3, 4, or 5, where the radicals R³ may be identical    or different, are novel.

Preferred are biphenylbenzamide derivatives of the formula (Ia), inwhich

-   R¹ represents trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³ represents halogen, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio,    C₂–C₄-alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or    represents C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or C₁–C₄-haloalkylthio    having in each case 1 to 9 halogen atoms,-   n represents 2, 3, where the radicals R³ may be identical or    different.

Particularly preferred are biphenylbenzamide derivatives of the formula(Ia), in which

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,    n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, or represents C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or    C₁–C₂-haloalkylthio having in each case 1 to 5 halogen atoms,-   n represents 2, where the radicals R³ can be identical or different.

Very particularly preferred are biphenylbenzamide derivatives of theformula (Ia), in which

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³ represents fluorine, chlorine, bromine, methyl, methoxy,    methylthio, trifluoromethyl, trifluoromethoxy or    trifluoromethylthio,-   n represents 2, where the radicals R³ can be identical or different.

Also novel are biphenylbenzamide derivatives of the formula (Ib) (group2)

in which

-   R¹ represents methyl, trifluoromethyl, chlorine, bromine or iodine,-   R²⁰ represents fluorine,-   R³ represents halogen, cyano, nitro, C₁–C₆-alkyl, C₁–C₄-alkoxy,    C₁–C₄-alkylthio, C₁–C₄-alkylsulphonyl, C₂–C₆-alkenyl,    C₃–C₆-cycloalkyl, or represents C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy,    C₁–C₆-haloalkylthio or C₁–C₆-haloalkylsulphonyl having in each case    1 to 13 halogen atoms,-   m represents 1, 2, 3, 4 or 5, where the radicals R³ may be identical    or different if m represents 2, 3, 4 or 5.

Preferred are biphenylbenzamide derivatives of the formula (Ib), inwhich

-   R¹ represents trifluoromethyl, chlorine, bromine or iodine,-   R²⁰ represents fluorine,-   R³ represents halogen, C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio,    C₂–C₄-alkenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or    represents C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or C₁–C₄-haloalkylthio    having in each case 1 to 9 halogen atoms,-   m represents 1, 2, 3, where the radicals R³ may be identical or    different if m represents 2 or 3.

Particularly preferred are biphenylbenzamide derivatives of the formula(Ib), in which

-   R¹ represents trifluoromethyl or iodine,-   R²⁰ represents fluorine,-   R³ represents fluorine, chlorine, bromine, iodine, methyl, ethyl,    n-, i-propyl, n-, i-, s-, t-butyl, methoxy, ethoxy, methylthio,    ethylthio, or represents C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or    C₁–C₂-haloalkylthio having in each case 1 to 5 halogen atoms,-   m represents 1, 2, where the radicals R³ can be identical or    different if m represents 2.

Very particularly preferred are biphenylbenzamide derivatives of theformula (Ib), in which

-   R¹ represents trifluoromethyl or iodine,-   R²⁰ represents fluorine,-   R³ represents fluorine, chlorine, bromine, methyl, methoxy,    methylthio, trifluoromethyl, trifluoromethoxy or    trifluoromethylthio,-   m represents 1, 2, where the radicals R³ can be identical or    different if m represents 2.

Also novel are biphenylbenzamide derivatives of the formulae (Ic) (group3), (Id) (group 4) and (Ie) (group 5)

in which in each case

-   R¹ represents methyl, trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³¹, R³² and R³³ independently of one another represent halogen,    cyano, nitro, C₁–C₆-allyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio,    C₁–C₄-alkylsulphonyl, C₂–C₆-alkenyl, C₃–C₆-cycloalkyl, or represent    C₁–C₆-haloalkyl, C₁–C₆-haloalkoxy, C₁–C₆-haloalkylthio or    C₁–C₆-haloalkylsulphonyl having in each case 1 to 13 halogen atoms,    with the proviso that R³¹ and R³³ each do not represent fluorine if    R¹ represents trifluoromethyl and R² represents hydrogen.

Preferred are biphenylbenzamide derivatives of the formulae (Ic), (Id)and (Ie), in which in each case

-   R¹ represents trifluoromethyl, chlorine, bromine or iodine,-   R² represents hydrogen or fluorine,-   R³¹, R³² and R³³ independently of one another represent halogen,    C₁–C₄-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₂–C₄-alkenyl,    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or represent    C₁–C₄-haloalkyl, C₁–C₄-haloalkoxy or C₁–C₄-haloalkylthio having in    each case 1 to 9 halogen atoms,    with the proviso that R³¹ and R³³ each do not represent fluorine if    R¹ represents trifluoromethyl and R² represents hydrogen.

Particularly preferred are biphenylbenzamide derivatives of the formulae(Ic), (Id) and (Ie), in which in each case

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³¹, R³² and R³³ independently of one another represent fluorine,    chlorine, bromine, iodine, methyl, ethyl, n-, i-propyl, n-, i-, s-,    t-butyl, methoxy, ethoxy, methylthio, ethylthio, or represent    C₁–C₂-haloalkyl, C₁–C₂-haloalkoxy or C₁–C₂-haloalkylthio having in    each case 1 to 5 halogen atoms,    with the proviso that R³¹ and R³³ each do not represent fluorine if    R¹ represents trifluoromethyl and R² represents hydrogen.

Very particularly preferred are biphenylbenzamide derivatives of theformulae (Ic), (Id) and (Ie), in which in each case

-   R¹ represents trifluoromethyl or iodine,-   R² represents hydrogen,-   R³¹, R³² and R³³ independently of one another represent fluorine,    chlorine, bromine, methyl, methoxy, methylthio, trifluoromethyl,    trifluoromethoxy or trifluoromethylthio,    with the proviso that R³¹ and R³³ each do not represent fluorine if    R¹ represents trifluoromethyl and R² represents hydrogen.

Furthermore, it has been found that the novel biphenylbenzamidederivatives of the formulae (Ia), (Ib), (Ic), (Id) and (Ie) have verygood microbicidal properties and can be used both in crop protection andin the protection of materials for controlling unwanted microorganisms.

The general or preferred radical definitions or illustrations givenabove can also be combined with one another as desired, i.e. includingcombinations between the respective ranges and preferred ranges. Thedefinitions apply both to the end products and, correspondingly, toprecursors and intermediates. Moreover, individual definitions may notapply.

Saturated hydrocarbon radicals, such as alkyl, can in each case bestraight-chain or branched as far as this is possible, including incombination with heteroatoms, such as, for example, in alkoxy.

Halogen-substituted radicals, for example haloalkyl, are mono- orpolyhalogenated up to the maximum possible number of substituents. Inthe case of polyhalogenation, the halogen atoms can be identical ordifferent. Here, halogen represents fluorine, chlorine, bromine oriodine, in particular fluorine, chlorine or bromine.

Biphenylbenzamide derivatives of the formulae (Ia), (Ib), (Ic), (Id) and(Ie) are in each case sub-groups of the compounds of the formula (I)which can be used according to the invention. In principle, thesecompounds can be prepared by the same route. Accordingly, thepreparation of the compounds of the formula (I) is described hereinbelowby way of example.

Compounds of the formula (I) can be prepared by

-   A) reacting benzoyl halides of the formula (II)

-   -   in which    -   R¹ is as defined above,    -   X¹ represents halogen,    -   with aniline derivatives of the formula (III)

-   -   in which    -   R², R³ and m are as defined above,    -   if appropriate in the presence of an acid binder and if        appropriate in the presence of a diluent, or

-   B) reacting halobenzainides of the formula (IV)

-   -   in which    -   R¹ and R² are as defined above,    -   X² represents bromine or iodine,    -   with boronic acid derivatives of the formula (V)

-   -   in which    -   R³ and m are as defined above,    -   G¹ and G² each represent hydrogen or together represent        tetramethylethylene    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or

-   C) reacting benzamide boronic acid derivatives of the formula (VI)

-   -   in which    -   R¹ and R² are as defined above,    -   G³ and G⁴ each represent hydrogen or together represent        tetramethylethylene    -   with halobenzene derivatives of the formula (VII)

-   -   in which    -   R³ and m are as defined above and    -   X³ represents bromine, iodine or trifluoromethylsulphonyloxy,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent,        or

-   D) reacting halobenzamides of the formula (IV)

-   -   in which    -   R¹ and R² are as defined above,    -   X² represents bromine or iodine,    -   in a first step with a diborane derivative of the formula (VIII)

-   -   in which    -   G⁵ and G⁶ each represent alkyl or together represent alkanediyl,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent        and, without work-up, in a second step with halobenzene        derivatives of the formula (VII)

-   -   in which    -   R³ and m are as defined above and    -   X³ represents bromine, iodine or trifluoromethylsulphonyloxy,    -   in the presence of a catalyst, if appropriate in the presence of        an acid binder and if appropriate in the presence of a diluent.

Using, for example, 2-(trifluoromethyl)benzoyl chloride and4′-chloro-1,1′-biphenyl-2-amine as starting materials and a base, thecourse of the process A) according to the invention can be illustratedby the following equation:

The formula (II) provides a general definition of the benzoyl halidesrequired as starting materials for carrying out the process A) accordingto the invention. In this formula (II), R¹ preferably, particularlypreferably and very particularly preferably has those meanings whichhave already been mentioned in connection with the description of thecompounds of the formula (I) which can be used according to theinvention as being preferred, particularly preferred, etc., for thisradical. X¹ preferably represents chlorine.

The benzoyl halides of the formula (II) are known and/or can be preparedby known processes (compare, for example EP-A 0 276 177).

The formula (III) provides a general definition of the anilinederivatives furthermore required as starting materials for carrying outthe process A) according to the invention. In this formula (III), R², R³and m preferably, particularly preferably and very particularlypreferably have those meanings which have already been mentioned inconnection with the description of the compounds of the formula (I)which can be used according to the invention as being preferred,particularly preferred, etc., for these radicals.

The aniline derivatives of the formula (III) are known and/or can beprepared by known methods (cf., for example, Bull. Korean Chem. Soc.2000 21, 165–166; Chem. Pharm. Bull. 1992, 40, 240–4; JP 9132567).

Using, for example, N-(2-iodophenyl)-2-(trifluoromethyl)benzamide and4-chlorophenylboronic acid as starting materials and a catalyst and abase, the course of the process B) according to the invention can beillustrated by the following equation:

The formula (IV) provides a general definition of the halobenzamidesrequired as starting materials for carrying out the process B) accordingto the invention. In this formula (IV), R¹ and R² preferably,particularly preferably and very particularly preferably have thosemeanings which have already been mentioned in connection with thedescription of the compounds of the formula (I) which can be usedaccording to the invention as being preferred, particularly preferred,etc., for these radicals. X² preferably represents bromine or iodine.

The halobenzamides of the formula (IV) have hitherto not been disclosed.They are novel chemical compounds and also form part of thesubject-matter of the present application. They are obtained by

-   E) reacting benzoyl halides of the formula (II)

-   -   in which    -   R¹ is as defined above,    -   X¹ represents halogen,    -   with 2-bromoaniline or 2-iodoaniline.

The benzoyl halides of the formula (II) required as starting materialsfor carrying out the process E) according to the invention have alreadybeen described further above, in connection with process A) according tothe invention.

The compounds 2-bromoaniline and 2-iodoaniline furthermore required asstarting materials for carrying out the process E) according to theinvention are known chemicals for synthesis.

The formula (V) provides a general definition of the boronic acidderivatives furthermore required as starting materials for carrying outthe process B) according to the invention. In this formula (V), R³ and mpreferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) which can be usedaccording to the invention as being preferred, particularly preferred,etc., for these radicals. G¹ and G² preferably each represent hydrogenor together represent tetramethylethylene.

Boronic acid derivatives of the formula (V) are known chemicals forsynthesis. They can also be prepared directly, immediately prior to thereaction, from halobenzene derivatives and boronic acid esters, andreacted further without any work-up.

Using, for example,N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2-(trifluoromethyl)benzamideand 4-chlorophenyltrifluoromethanesulphonic acid as starting materialsand a catalyst and a base, the course for the process C) according tothe invention can be illustrated by the following equation:

The formula (VI) provides a general definition of the benzamide boronicacid derivatives required as starting materials for carrying out theprocess C) according to the invention. In this formula (VI), R¹ and R²preferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of compounds of the formula (I) which c an b e usedaccording to the invention as being preferred, particularly preferred,etc., for these radicals. G³ and G⁴ preferably each represent hydrogenor together represent tetramethylethylene.

The benzamide boronic acid derivatives of the formula (VI) have hithertonot been disclosed. They are novel chemical compounds and also form partof the subject-matter of the present application.

They are obtained by

-   F) reacting benzoyl halides of the formula (II)

-   -   in which    -   R¹ is as defined above,    -   X¹ represents halogen,    -   with aniline boronic derivatives of the formula (IX)

-   -   in which    -   G³ and G⁴ are as defined above,    -   if appropriate in the presence of an acid binder and if        appropriate in the presence of a diluent.

The benzoyl halides of the formula (II) required as starting materialsfor carrying out the process F) according to the invention have alreadybeen described above in connection with the process A) according to theinvention.

The formula (IX) provides a general definition of the anilineboronicacid derivatives furthermore required as starting materials for carryingout the process F) according to the invention. In this formula (IX), G³and G⁴ preferably each represent hydrogen or together representtetramethylethylene.

The anilineboronic acid derivatives of the formula (IX) required asstarting materials for carrying out the process F) according to theinvention are known chemicals for synthesis.

The formula (VII) provides a general definition of the halobenzenederivatives furthermore required as starting materials for carrying outthe process C) according to the invention. In this formula (VII), R³ andm preferably, particularly preferably and very particularly preferablyhave those meanings which have already been mentioned in connection withthe description of the compounds of the formula (I) which can be usedaccording to the invention as being preferred, particularly preferred,etc., for these radicals. X³ preferably represents bromine, iodine ortrifluoromethylsulphonyloxy.

Using, for example, N-(2-bromophenyl)-2-(trifluoromethyl)benzamide and4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bis-1,3,2-dioxaborolane in the firststep and furthermore 4-bromo-1-chloro-2-methylbenzene in the second stepas starting materials and in each step a catalyst and a base, the courseof the process D) according to the invention can be illustrated by thefollowing equation:

The halobenzamides of the formula (IV) required as starting materialsfor carrying out the process D) according to the invention have alreadybeen described above in connection with process B) according to theinvention.

The formula (VIII) provides a general definition of the diboranederivatives furthermore required as starting materials for carrying outthe process D) according to the invention. In this formula (VIII), G⁵and G⁶ preferably each represent methyl, ethyl, propyl, butyl ortogether represent tetramethylethylene.

The diborane derivatives of the formula (VIII) are generally knownchemicals for synthesis.

The halobenzene derivatives of the formula (VII) furthermore required asstarting materials for carrying out the process D) according to theinvention have already been described above, in connection with theprocess C) according to the invention.

Suitable diluents for carrying out the processes A), E) and F) accordingto the invention are all inert organic solvents. These preferablyinclude aliphatic, alicyclic or aromatic hydrocarbons, such as, forexample, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; halogenatedhydrocarbons, such as, for example, chlorobenzene, dichlorobenzene,dichloro-methane, chloroform, carbon tetrachloride, dichloroethane ortrichloroethane; ethers, such as diethyl ether, diisopropyl ether,methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran,1,2-dimethoxyethane, 1,2-diethoxyethane or anisole, or amides, such asN,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide,N-methylpyrrolidone or hexamethylphosphoric triamide.

The processes A), E) and F) according to the invention are, ifappropriate, carried out in the presence of a suitable acid acceptor.Suitable acid acceptors are all customary inorganic or organic bases.These preferably include alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates,such as, for example, sodium hydride, sodium amide, sodium methoxide,sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassiumhydroxide, ammonium hydroxide, sodium acetate, potassium acetate,calcium acetate, ammonium acetate, sodium carbonate, potassiumcarbonate, potassium bicarbonate, sodium bicarbonate or caesiumcarbonate, and also tertiary amines, such as trimethylamine,triethylamine, tributylamine, N,N-dimethylaniline,N,N-dimethyl-benzylamine, pyridine, N-methylpiperidine,N-methylmorpholine, N,N-dimethyl-aminopyridine, diazabicyclooctane(DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out the processes A), E) and F) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperatures offrom 0° C. to 150° C., preferably at temperatures of from 20° C. to 110°C.

For carrying out the process A) according to the invention for preparingthe compounds of the formula (I), in general from 0.2 to 5 mol,preferably from 0.5 to 2 mol, of the aniline derivative of the formula(III) are employed per mole of the benzoyl halide of the formula (II).Work-up is carried out by customary methods.

For carrying out the process E) according to the invention for preparingcompounds of the formula (III), in general from 0.2 to 5 mol, preferablyfrom 0.5 to 2 mol, of 2-bromoaniline or 2-iodoaniline are employed permole of the benzoyl halide of the formula (II). Work-up is carried outby customary methods.

For carrying out the process F) according to the invention for preparingthe compounds of the formula (VI), in general from 0.2 to 5 mol,preferably from 0.5 to 2 mol, of the aniline boronic acid derivative ofthe formula (IX) are employed per mole of the benzoyl halide of theformula (II). Work-up is carried out by customary methods.

Suitable diluents for carrying out the processes B), C) and D) accordingto the invention are all inert organic solvents. These preferablyinclude aliphatic, alicyclic or aromatic hydrocarbons, such as, forexample, petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; ethers, such asdiethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amylether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethaneor anisole; nitriles, such as acetonitrile, propionitrile, n- ori-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters, such methyl acetate or ethylacetate; sulphoxides, such as dimethyl sulphoxide; sulphones, such assulpholane; alcohols, such as methanol, ethanol, n- or i-propanol, n-,i-, sec- or tert-butanol, ethanediol, propane-1,2-diol, ethoxyethanol,methoxyethanol, diethylene glycol monomethyl ether, diethylene glycolmonoethyl ether, mixtures thereof with water or pure water.

When carrying out the processes B), C) and D) according to theinvention, the reaction temperatures can be varied within a relativelywide range. In general, the processes are carried out at temperatures offrom 0° C. to 150° C., preferably at temperatures of from 20° C. to 110°C.

The processes B), C) and D) according to the invention are, ifappropriate, carried out in the presence of a suitable acid acceptor.Suitable acid acceptors are all customary inorganic or organic bases.These preferably include alkaline earth metal or alkali metal hydrides,hydroxides, amides, alkoxides, acetates, fluorides, phosphates,carbonates or bicarbonates, such as, for example, sodium hydride, sodiumamide, lithium diisopropylamide, sodium methoxide, sodium ethoxide,potassium tert-butoxide, sodium hydroxide, potassium hydroxide, sodiumacetate, sodium phosphate, potassium phosphate, potassium fluoride,caesium fluoride, sodium carbonate, potassium carbonate, potassiumbicarbonate, sodium bicarbonate or caesium carbonate, and also tertiaryamines, such as trimethylamine, triethylamine, tributylamine,N,N-dimethylaniline, N,N-dimethylbenzylamine, pyridine,N-methyl-piperidine, N-methylmorpholine, N,N-dimethylaminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiazabicycloundecene (DBU).

The processes B), C) and D) according to the invention are carried outin the presence of a catalyst, such as, for example, a palladium salt orcomplex. Preferably used for this purpose are palladium chloride,palladium acetate, tetrakis(triphenyl-phosphine)palladium,bis(triphenylphosphine)palladium dichloride or(1,1′-bis(diphenylphosphino)ferrocenepalladium(II) chloride).

It is also possible to generate a palladium complex in the reactionmixture by separate addition of a palladium salt and a complex ligand,such as, for example, triethyl-phosphine, tri-tert-butylphosphine,tricyclohexylphosphine, 2-(dicyclohexyl-phosphine)biphenyl,2-(di-tert-butylphosphine)biphenyl,2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)biphenyl,triphenylphosphine, tris-(o-tolyl)phosphine, sodium3-(diphenylphosphino)benzenesulphonate,tris-2-(methoxyphenyl)-phosphine,2,2′-bis(diphenylphosphine)-1,1′-binaphthyl,1,4-bis(diphenylphosphine)-butane, 1,2-bis(diphenylphosphine)ethane,1,4-bis(dicyclohexylphosphine)butane,1,2-bis(dicyclohexylphosphine)ethane,2-(dicyclohexylphosphine)-2′-(N,N-dimethyl-amino)biphenyl,bis(diphenylphosphino)ferrocene or tris-(2,4-tert-butyl-phenyl)phosphiteto the reaction.

For carrying out the process B) according to the invention for preparingthe compounds of the formula (I), in general from 1 to 15 mol,preferably from 2 to 8 mol, of the boronic acid derivative of theformula (V) are employed per mole of the halobenzamide of the formula(IV). Work-up is carried out by customary methods.

For carrying out the process C) according to the invention for preparingthe compounds of the formula (I), in general from 1 to 15 mol,preferably from 2 to 8 mol, of halobenzene derivative of the formula(VII) are employed per mole of the benzamide boronic acid derivative ofthe formula (VI). Work-up is carried out by customary methods.

For carrying out the process D) according to the invention for preparingthe compounds of the formula (I), in general from 1 to 15 mol,preferably from 1 to 5 mol, of diborane derivative of the formula (VIII)and from 1 to 15 mol, preferably from 1 to 5 mol, of halobenzenederivative of the formula (VII) are employed per mole of the halobenzenederivative of the formula (IV).

The processes A), B), C), D), E) and F) according to the invention aregenerally carried out under atmospheric pressure. However, it is alsopossible to operate under elevated or reduced pressure—in generalbetween 0.1 bar and 10 bar.

The active compounds of the formulae (Ia), (Ib), (Ic), (Id) and (Ie)according to the invention have potent microbicidal activity and can beemployed for controlling undesirable microorganisms, such as fungi andbacteria, in crop protection and in the protection of materials.

Fungicides can be employed in crop protection for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

Bactericides can be employed in crop protection for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

Some pathogens causing fungal and bacterial diseases which come underthe generic names listed above may be mentioned as examples, but not byway of limitation:

Xanthomonas species, such as, for example, Xanthomonas campestris pv.oryzae;

-   Pseudomonas species, such as, for example, Pseudomonas syringae pv.    lachrymans;-   Erwinia species, such as, for example, Erwinia amylovora;-   Pythium species, such as, for example, Pythium ultimum;-   Phytophthora species, such as, for example, Phytophthora infestans;-   Pseudoperonospora species, such as, for example, Pseudoperonospora    humuli or Pseudoperonospora cubensis;-   Plasmopara species, such as, for example, Plasmopara viticola;-   Bremia species, such as, for example, Bremia lactucae;-   Peronospora species, such as, for example, Peronospora pisi or P.    brassicae;-   Erysiphe species, such as, for example, Erysiphe graminis;-   Sphaerotheca species, such as, for example, Sphaerotheca fuliginea;-   Podosphaera species, such as, for example, Podosphaera leucotricha;-   Venturia species, such as, for example, Venturia inaequalis;-   Pyrenophora species, such as, for example, Pyrenophora teres or P.    graminea (conidia form: Drechslera, syn: Helminthosporium);-   Cochliobolus species, such as, for example, Cochliobolus sativus    (conidia form: Drechslera, syn: Helminthosporium);-   Uromyces species, such as, for example, Uromyces appendiculatus;-   Puccinia species, such as, for example, Puccinia recondita;-   Sclerotinia species, such as, for example, Sclerotinia sclerotiorum;-   Tilletia species, such as, for example, Tilletia caries;-   Ustilago species, such as, for example, Ustilago nuda or Ustilago    avenae;-   Pellicularia species, such as, for example, Pellicularia sasakii;-   Pyricularia species, such as, for example, Pyricularia oryzae;-   Fusarium species, such as, for example, Fusarium culmorum;-   Botrytis species, such as, for example, Botrytis cinerea;-   Uncinula species, such as, for example, Uncinula necator;-   Septoria species, such as, for example, Septoria nodorum;-   Leptosphaeria species, such as, for example, Leptosphaeria nodorum;-   Cercospora species, such as, for example, Cercospora canescens;-   Alternaria species, such as, for example, Alternaria brassicae; and-   Pseudocercosporella species, such as, for example,    Pseudocercosporella herpotrichoides.

The active compounds of the formulae (Ia), (Ib), (Ic), (Id) and (Ie)according to the invention also show a strong invigorating action inplants. Accordingly, they are suitable for mobilizing the internaldefences of the plant against attack by unwanted microorganisms.

In the present context, plant-invigorating (resistance-inducing)compounds are to be understood as meaning substances which are capableof stimulating the defence system of plants such that, when the treatedplants are subsequently inoculated with unwanted microorganisms, theydisplay substantial resistance to these microorganisms.

In the present case, unwanted microorganisms are to be understood asmeaning phytopathogenic fungi, bacteria and viruses. The compoundsaccording to the invention can thus be used to protect plants within acertain period of time after treatment against attack by the pathogensmentioned. The period of time for which this protection is achievedgenerally extends for 1 to 10 days, preferably 1 to 7 days, from thetreatment of the plants with the active compounds.

The fact that the active compounds are well tolerated by plants at theconcentrations required for controlling plant diseases permits thetreatment of above-ground parts of plants, of propagation stock andseeds, and of the soil.

The active compounds of the formulae (Ia), (Ib), (Ic), (Id) and (Ie)according to the invention are also suitable for increasing the yield ofcrops. In addition, they show reduced toxicity and are well tolerated byplants.

If appropriate, the active compounds of the formulae (Ia), (Ib), (Ic),(Id) and (Ie) according to the invention can, at certain concentrationsand application rates, also be employed as herbicides, for regulatingplant growth and for controlling animal pests. If appropriate, they canalso be used as intermediates or precursors in the synthesis of otheractive compounds.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations, such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested material and vegetative and generative propagation material,for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to theinvention with the active compounds of the formulae (Ia), (Ib), (Ic),(Id) and (Ie) is carried out directly or by action on their environment,habitat or storage area according to customary treatment methods, forexample by dipping, spraying, evaporating, atomizing, broadcasting,brushing-on and, in the case of propagation material, in particular inthe case of seeds, furthermore by one- or multi-layer coating.

In the protection of materials, the compounds of the formulae (Ia),(Ib), (Ic), (Id) and (Ie) according to the invention can be employed forprotecting industrial materials against infection with, and destructionby, undesired microorganisms.

Industrial materials in the present context are understood as meaningnon-living materials which have been prepared for use in industry. Forexample, industrial materials which are intended to be protected byactive compounds according to the invention from microbial change ordestruction can be tackifiers, sizes, paper and board, textiles,leather, wood, paints and plastic articles, cooling lubricants and othermaterials which can be infected with, or destroyed by, microorganisms.Parts of production plants, for example cooling-water circuits, whichmay be impaired by the proliferation of microorganisms may also bementioned within the scope of the materials to be protected. Industrialmaterials which may be mentioned within the scope of the presentinvention are preferably tackifiers, sizes, paper and board, leather,wood, paints, cooling lubricants and heat-transfer liquids, particularlypreferably wood.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae.

Microorganisms of the following genera may be mentioned as examples:

-   Alternaria, such as Alternaria tenuis,-   Aspergillus, such as Aspergillus niger,-   Chaetomium, such as Chaetomium globosum,-   Coniophora, such as Coniophora puetana,-   Lentinus, such as Lentinus tigrinus,-   Penicillium, such as Penicillium glaucum,-   Polyporus, such as Polyporus versicolor,-   Aureobasidium, such as Aureobasidium pullulans,-   Sclerophoma, such as Sclerophoma pityophila,-   Trichoderma, such as Trichoderma viride,-   Escherichia, such as Escherichia coli,-   Pseudomonas, such as Pseudomonas aeruginosa, and-   Staphylococcus, such as Staphylococcus aureus.

Depending on their particular physical and/or chemical properties, theactive compounds can be converted into the customary formulations, suchas solutions, emulsions, suspensions, powders, foams, pastes, granules,aerosols and microencapsulations in polymeric substances and in coatingcompositions for seeds, and ULV cool and warm fogging formulations.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is liquid solvents, liquefiedgases under pressure, and/or solid carriers, optionally with the use ofsurfactants, that is emulsifiers and/or dispersants, and/or foamformers. If the extender used is water, it is also possible to employ,for example, organic solvents as auxiliary solvents. Essentially,suitable liquid solvents are: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample petroleum fractions, alcohols such as butanol or glycol andtheir ethers and esters, ketones such as acetone, methyl ethyl ketone,methyl isobutyl ketone or cyclohexanone, strongly polar solvents such asdimethylformamide or dimethyl sulphoxide, or else water. Liquefiedgaseous extenders or carriers are to be understood as meaning liquidswhich are gaseous at standard temperature and under atmosphericpressure, for example aerosol propellants such as halogenatedhydrocarbons, or else butane, propane, nitrogen and carbon dioxide.

Suitable solid carriers are: for example ground natural minerals such askaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite ordiatomaceous earth, and ground synthetic minerals such as finely dividedsilica, alumina and silicates. Suitable solid carriers for granules are:for example crushed and fractionated natural rocks such as calcite,marble, pumice, sepiolite and dolomite, or else synthetic granules ofinorganic and organic meals, and granules of organic material such assawdust, coconut shells, maize cobs and tobacco stalks. Suitableemulsifiers and/or foam formers are: for example nonionic and anionicemulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylenefatty alcohol ethers, for example alkylaryl polyglycol ethers,alkylsulphonates, alkyl sulphates, arylsulphonates, or else proteinhydrolysates. Suitable dispersants are: for example lignosulphite wasteliquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs suchas alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention can, as such or in theirformulations, also be used in a mixture with known fungicides,bactericides, acaricides, nematicides or insecticides, to broaden, forexample, the activity spectrum or to prevent development of resistance.In many cases, synergistic effects are obtained, i.e. the activity ofthe mixture is greater than the activity of the individual components.

Suitable mixing components are, for example, the following compounds:

Fungicides:

-   2-phenylphenol; 8-hydroxyquinoline sulphate;-   acibenzolar-S-methyl; aldimorph; amidoflumet; ampropylfos;    ampropylfos-potassium;-   andoprim; anilazine; azaconazole; azoxystrobin;-   benalaxyl; benodanil; benomyl; benthiavalicarb-isopropyl;    benzamacril; benzamacril-isobutyl;-   bilanafos; binapacryl; biphenyl; bitertanol; blasticidin-S;    bromuconazole;-   bupirimate; buthiobate; butylamine;-   calcium polysulphide; capsimycin; captafol; captan; carbendazim;    carboxin;-   carpropamid; carvone; chinomethionat; chlobenthiazone;    chlorfenazole; chloroneb;-   chlorothalonil; chlozolinate; clozylacon; cyazofamid; cyflufenamid;    cymoxanil;-   cyproconazole; cyprodinil; cyprofuram;-   Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;    diclocymet; diclomezine;-   dicloran; diethofencarb; difenoconazole; diflumetorim; dimethirimol;-   dimethomorph; dimoxystrobin; diniconazole; diniconazole-M; dinocap;    diphenylamine;-   dipyrithione; ditalimfos; dithianon; dodine; drazoxolon;-   edifenphos; epoxiconazole; ethaboxam; ethirimol; etridiazole;-   famoxadone; fenamidone; fenapanil; fenarimol; fenbuconazole;    fenfuram; fenhexamid;-   fenitropan; fenoxanil; fenpiclonil; fenpropidin; fenpropimorph;    ferbam;-   fluazinam; flubenzinine; fludioxonil; flumetover; flumorph;    fluoromide;-   fluoxastrobin; fluquinconazole; flurprimidol; flusilazole;    flusulfamide; flutolanil;-   flutriafol; folpet; fosetyl-Al; fosetyl-sodium; fuberidazole;    furalaxyl; furametpyr;-   furcarbanil; furmecyclox;-   guazatine; hexachlorobenzene; hexaconazole; hymexazole;-   imazalil; imibenconazole; iminoctadine triacetate; iminoctadine    tris(albesil);-   iodocarb; ipconazole; iprobenfos; iprodione; iprovalicarb;    irumamycin;-   isoprothiolane; isovaledione;-   kasugamycin; kresoxim-methyl;-   mancozeb; maneb; meferimzone; mepanipyrim; mepronil; metalaxyl;    metalaxyl-M;-   metconazole; methasulfocarb; methfuroxam; metiram; metominostrobin;    metsulfovax;-   mildiomycin; myclobutanil; myclozolin;-   natamycin; nicobifen; nitrothal-isopropyl; noviflumuron; nuarimol;-   ofurace; orysastrobin; oxadixyl; oxolinic acid; oxpoconazole;    oxycarboxin;-   oxyfenthiin;-   paclobutrazole; pefurazoate; penconazole; pencycuron; phosdiphen;    phthalide; picoxystrobin;-   piperalin; polyoxins; polyoxorim; probenazole; prochloraz;    procymidone;-   propamocarb; propanosine-sodium; propiconazole; propineb;    proquinazid; prothioconazole;-   pyraclostrobin; pyrazophos; pyrifenox; pyrimethanil; pyroquilon;-   pyroxyfur; pyrrolenitrine;-   quinconazole; quinoxyfen; quintozene;-   simeconazole; spiroxamine; sulphur;-   tebuconazole; tecloftalam; tecnazene; tetcyclacis; tetraconazole;    thiabendazole;-   thicyofen; thifluzamide; thiophanate-methyl; thiram; tioxymid;    tolclofos-methyl;-   tolylfluanid; triadimefon; triadimenol; triazbutil; triazoxide;    tricyclamide; tricyclazole;-   tridemorph; trifloxystrobin; triflumizole; triforine; triticonazole;-   uniconazole; validamycin A; vinclozolin;-   zineb; ziram; zoxamide;-   (2S)-N-[2-[4-[[3-(4-chlorophenyl)-2-propynyl]oxy]-3-methoxyphenyl]ethyl]-3-methyl-2-[(methylsulphonyl)amino]butanamide;    1-(1-naphthalenyl)-1H-pyrrole-2,5-dione;    2,3,5,6-tetrachloro-4-(methylsulphonyl)pyridine;    2-amino-4-methyl-N-phenyl-5-thiazolecarboxamide;    2-chloro-N-(2,3-dihydro-1,1,3-trimethyl-1H-inden-4-yl)-3-pyridinecarboxamide;    3,4,5-trichloro-2,6-pyridinedicarbonitrile; actinovate;    cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol;    methyl    1-(2,3-dihydro-2,2-dimethyl-1H-inden-1-yl)-1H-imidazole-5-carboxylate;    monopotassium carbonate;    N-(6-methoxy-3-pyridinyl)-cyclopropanecarboxamide;    N-butyl-8-(1,1-dimethyl-ethyl)-1-oxaspiro[4.5]decane-3-amine; sodium    tetrathiocarbonate;-   and copper salts and preparations, such as Bordeaux mixture; copper    hydroxide;-   copper naphthenate; copper oxychloride; copper sulphate; cufraneb;    copper oxide; mancopper; oxine-copper.    Bactericides:-   bronopol, dichlorophen, nitrapyrin, nickel dimethyldithiocarbamate,    kasugamycin, octhilinone, furancarboxylic acid, oxytetracyclin,    probenazole, streptomycin, tecloftalam, copper sulphate and other    copper preparations.    Insecticides/acaricides/nematicides:-   abanectin, ABG-9008, acephate, acequinocyl, acetamiprid, acetoprole,    acrinathrin, AKD-1022, AKD-3059, AKD-3088, alanycarb, aldicarb,    aldoxycarb, allethrin, allethrin 1R-isomers, alpha-cypermethrin    (alphamethrin), amidoflumet, aminocarb, amitraz, avermectin,    AZ-60541, azadirachtin, azamethiphos, azinphos-methyl,    azinphos-ethyl, azocyclotin,-   Bacillus popilliae, Bacillus sphaericus, Bacillus subtilis, Bacillus    thuringiensis, Bacillus thuringiensis strain EG-2348, Bacillus    thuringiensis strain GC-91, Bacillus thuringiensis strain    NCTC-11821, 0baculoviruses, Beauveria bassiana, Beauveria tenella,    bendiocarb, benfuracarb, bensultap, benzoximate, beta-cyfluthrin,    beta-cyper-methrin, bifenazate, bifenthrin, binapacryl,    bioallethrin, bioallethrin-S-cyclopentyl-isomer, bioethanomethrin,    biopermethrin, bioresmethrin, bistrifluron, BPMC, brofen-prox,    bromophos-ethyl, bromopropylate, bromfenvinfos (-methyl), BTG-504,    BTG-505, bufencarb, buprofezin, butathiofos, butocarboxim,    butoxycarboxim, butyl-pyridaben,-   cadusafos, camphechlor, carbaryl, carbofuran, carbophenothion,    carbosulfan, cartap, CGA-50439, chinomethionat, chlordane,    chlordimeform, chloethocarb, chlorethoxyfos, chlorfenapyr,    chlorfenvinphos, chlorfluazuron, chlonnephos, chlorobenzilate,    chloropicrin, chlorproxyfen, chlorpyrifos-methyl, chlorpyrifos    (-ethyl), chlovaporthrin, chromafenozide, cis-cypermethrin,    cis-resmethrin, cis-permethrin, clocythrin, cloethocarb,    clofentezine, clothianidin, clothiazoben, codlemone, coumaphos,    cyanofenphos, cyanophos, cycloprene, cycloprothrin, Cydia pomonella,    cyfluthrin, cyhalothrin, cyhexatin, cypennethrin, cyphenothrin    (1R-trans-isomer), cyromazine, DDT, deltamethrin, demeton-S-methyl,    demeton-S-methylsulphone, diafenthiuron, dialifos, diazinon,    dichlofenthion, dichlorvos, dicofol, dicrotophos, dicyclanil,    diflubenzuron, dimethoate, dimethylvinphos, dinobuton, dinocap,    dinotefuran, diofenolan, disulfoton, docusat-sodium, dofenapyn,    DOWCO-439,-   eflusilanate, emamectin, emamectin-benzoate, empenthrin (1R-isomer),    endosulfan, Entomopthora spp., EPN, esfenvalerate, ethiofencarb,    ethiprole, ethion, ethoprophos, etofenprox, etoxazole, etrimfos,-   famphur, fenamiphos, fenazaquin, fenbutatin oxide, fenfluthrin,    fenitrothion, fenobucarb, fenothiocarb, fenoxacrim, fenoxycarb,    fenpropathrin, fenpyrad, fenpyrithrin, fenpyroximate, fensulfothion,    fenthion, fentrifanil, fenvalerate, fipronil, flonicamid,    fluacrypyrim, fluazuron, flubenzimine, flubrocythrinate,    flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox,    flumethrin, flupyrazofos, flutenzin (flufenzine), fluvalinate,    fonofos, formetanate, formothion, fosmethilan, fosthiazate,    fubfenprox (fluproxyfen), fuirathiocarb,-   gamma-HCH, gossyplure, grandlure, granulosis viruses,-   halfenprox, halofenozide, HCH, HCN-801, heptenophos, hexaflumuron,    hexythiazox, hydramethylnone, hydroprene,-   IKA-2002, imidacloprid, imiprothrin, indoxacarb, iodofenphos,    iprobenfos, isazofos,-   isofenphos, isoprocarb, isoxathion, ivermectin,-   japonilure,-   kadethrin, nuclear polyhedrosis viruses, kinoprene,-   lambda-cyhalothrin, lindane, lufenuron,-   malathion, mecarbam, mesulfenfos, metaldehyde, metam-sodium,    methacrifos, methamidophos, Metharhizium anisopliae, Metharhizium    flavoviride, methidathion, methiocarb, methomyl, methoprene,    methoxychlor, methoxyfenozide, metolcarb, metoxadiazone, mevinphos,    milbemectin, milbemycin, MKI-245, MON-45700, monocrotophos,    moxidectin, MTI-800,-   naled, NC-104, NC-170, NC-184, NC-194, NC-196, niclosamide,    nicotine, nitenpyram, nithiazine, NNI-0001, NNI-0101, NNI-0250,    NNI-9768, novaluron, novi-flumuron,-   OK-5101, OK-5201, OK-9601, OK-9602, OK-9701, OK-9802, omethoate,    oxamyl, oxydemeton-methyl,-   Paecilomyces fuimosoroseus, parathion-methyl, parathion (-ethyl),    permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (1R-trans    isomer), phenthoate, phorate, phosalone, phosmet, phosphamidon,    phosphocarb, phoxim, piperonyl butoxide, pirimicarb,    pirimiphos-methyl, pirimiphos-ethyl, prallethrin, profenofos,    promecarb, propaphos, propargite, propetamphos, propoxur,    prothiofos, prothoate, protrifenbute, pymetrozine, pyraclofos,    pyresmethrin, pyrethrum, pyridaben, pyridalyl, pyridaphenthion,    pyridathion, pyrimidifen, pyriproxyfen, quinalphos,-   resmethrin, RH-5849, ribavirin, RU-12457, RU-15525,-   S-421, S-1833, salithion, sebufos, SI-0009, silafluofen, spinosad,    spirodiclofen, spiromesifen, sulfluramid, sulfotep, sulprofos,    SZI-121,-   tau-fluvalinate, tebufenozide, tebufenpyrad, tebupirimfos,    teflubenzuron, tefluthrin, temephos, temivinphos, terbam, terbufos,    tetrachlorvinphos, tetradifon, tetramethrin, tetramethrin    (lR-isomer), tetrasul, theta-cypermethrin, thiacloprid,    thiamethoxam, thiapronil, thiatriphos, thiocyclam hydrogenoxalate,    thiodicarb, thiofanox, thiometon, thiosultap-sodium, thuringiensin,    tolfenpyrad, tralocythrin, tralomethrin, transfluthrin, triarathene,    triazamate, triazophos, triazuron, trichlophenidine, trichlorfon,-   triflumuron, trimethacarb,-   vamidothion, vaniliprole, verbutin, Verticillium lecanii,-   WL-108477, WL-40027,-   YI-5201, YI-5301, YI-5302,-   XMC, xylylcarb,-   ZA-3274, zeta-cypermethrin, zolaprofos, ZXI-8901,-   the compound 3-methylphenyl propylcarbamate (tsumacide Z),-   the compound    3-(5-chloro-3-pyridinyl)-8-(2,2,2-trifluoroethyl)-8-azabicyclo[3.2.1]-octane-3-carbonitrile    (CAS-Reg. No. 185982-80-3) and the corresponding 3-endo-isomer    (CAS-Reg. No. 185984-60-5) (cf. WO-96/37494, WO-98/25923),-   and preparations which comprise insecticidally active plant    extracts, nematodes, fungi or viruses.

A mixture with other known active compounds, such as herbicides, or withfertilizers and growth regulators, safeners and/or semiochemicals isalso possible.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes,Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi does by no means limit the mycotic spectrum which can becovered, but is only for illustration.

The active compounds can be used as such, in the form of theirformulations or the use forms prepared therefrom, such as ready-to-usesolutions, suspensions, wettable powders, pastes, soluble powders, dustsand granules. Application is carried out in a customary manner, forexample by watering, spraying, atomizing, broadcasting, dusting,foaming, spreading, etc. It is furthermore possible to apply the activecompounds by the ultra-low volume method, or to inject the activecompound preparation or the active compound itself into the soil. It isalso possible to treat the seeds of the plants.

When using the active compounds according to the invention asfungicides, the application rates can be varied within a relatively widerange, depending on the kind of application. For the treatment of partsof plants, the active compound application rates are generally between0.1 and 10,000 g/ha, preferably between 10 and 1000 g/ha. For seeddressing, the active compound application rates are generally between0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 gper kilogram of seed. For the treatment of the soil, the active compoundapplication rates are generally between 0.1 and 10,000 g/ha, preferablybetween 1 and 5000 g/ha.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding, such as crossing or protoplast fusion, and partsthereof, are treated. In a further preferred embodiment, transgenicplants and plant cultivars obtained by genetic engineering, ifappropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The term “parts” or“parts of plants” or “plant parts” has been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention. Plant cultivars are to be understood as meaning plants havingnew properties (“traits”) and which have been obtained by conventionalbreeding, by mutagenesis or by recombinant DNA techniques. They can becultivars, varieties, bio- or genotypes.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferably treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, oilseed rape andalso fruit plants (with the fruits apples, pears, citrus fruits andgrapes), and particular emphasis is given to maize, soya beans,potatoes, cotton and oilseed rape. Traits that are emphasized are inparticular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”).

Traits that are also particularly emphasized are the increased defenceof the plants against fungi, bacteria and viruses by systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and resistance genesand correspondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulphonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes which impart the desired traits inquestion can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulphonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned also include thevarieties sold under the name Clearfield® (for example maize). Ofcourse, these statements also apply to plant cultivars having thesegenetic traits or genetic traits still to be developed, which plantswill be developed and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformulae (I), (Ia), (Ib), (Ic), (Id) and (Ie) or the active compoundmixtures according to the invention. The preferred ranges stated abovefor the active compounds or mixtures also apply to the treatment ofthese plants. Particular emphasis is given to the treatment of plantswith the compounds or mixtures specifically mentioned in the presenttext.

The preparation and the use of the active compounds according to theinvention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

Process A):

-   0.288 g (1.3 mmol) of 3′-chloro-4′-fluoro-1,1′-biphenyl-2-amine is    dissolved in 3 ml of tetrahydrofuran and 0.36 ml (2.6 mmol) of    triethylamine and 0.25 g (1.56 mmol) of 2-trifluoromethylbenzoyl    chloride (dissolved in 3 ml of tetrahydrofuran) are added. The    reaction solution is stirred at 60° C. for 16 h. For work-up, the    mixture is concentrated and the crude product is purified by column    chromatography (cyclohexane/ethyl acetate 2:1).

This gives 0.491 g (96% of theory) ofN-(3′-chloro-4′-fluoro-1,1′-biphenyl-2-yl)-2-(trifluoromethyl)benzamide(compound 35, cf. Table 1) of logP (pH 2.3)=3.81.

Example 2

Process D)

226 mg (1.1 mmol) of 2-chloro-5-bromotoluene, 245 mg (2.5 mmol) ofpotassium acetate and 279 m g (1.1 m mol) of pinacoldiboronic ester aredissolved in 8 ml of dimethylformamide (which contains as little oxygenas possible), and a catalytic amount (0.1 eq.) of PdCl₂(dppf) is added.The reaction mixture is stirred at 80–90° C. for 2 h and, after cooling,5 eq. of 2 M sodium carbonate solution, 344 mg (1.0 mmol) ofN-(2-bromophenyl)-2-(trifluoromethyl)benzamide (dissolved in 4 ml ofdimethylformamide) and a further 0.1 eq. of catalyst are added. Thereaction solution is stirred at 80–90° C. for 16 h. For work-up, 2 ml ofwater and 8 ml of ethyl acetate are added. The organic phase isconcentrated and purified by column chromatography (cyclohexane/ethylacetate 1:1).

This gives 151 mg (39% of theory) ofN-(4′-chloro-3′-methyl-1,1′-biphenyl-2-yl)-2-(trifluoromethyl)benzamide(compound 42, cf. Table 1) of logP (pH 2.3)=4.18.

The compounds of the formula (I) listed in Table 1 below can be obtainedanalogously to Examples 1 and 2 and in accordance with the generaldescriptions of the processes A) to D) according to the invention. Thelast column of the table states to which group of novel compoundsaccording to the invention the substance in question belongs.

TABLE 1 (I)

No. R¹ R² m R³ logP (pH 2.3) Group 1 CF₃ H 1 4-Cl 3.73 3 2 CF₃ H 22,4-Cl₂ 4.00 1 3 CF₃ H 2 2-CH₃, 4-Cl 4.14 1 4 CF₃ H 2 3,4-Cl₂ 4.13 1 5CF₃ H 1 4-Br 4.03 3 6 CF₃ H 1 4-CF₃ 4.05 3 7 CF₃ H 1 3-Cl 3.86 4 8 CF₃ H1 4-OCF₃ 4.20 3 9 CF₃ H 1 4-SCH₃ 3.89 3 10 Cl H 1 4-Br 3.89 3 11 Cl H 14-CF₃ 3.89 3 12 Cl H 1 3-Cl 3.75 4 13 Cl H 1 4-OCF₃ 4.08 3 14 Cl H 14-SCH₃ 3.75 3 15 Cl H 1 4-F 3.40 3 16 Br H 1 4-Br 3.91 3 17 Br H 1 4-CF₃3.94 3 18 Br H 1 3-Cl 3.78 4 19 Br H 1 4-OCF₃ 4.08 3 20 Br H 1 4-SCH₃3.78 3 21 Br H 1 4-F 3.42 3 22 CH₃ H 1 4-Br 3.86 3 23 CH₃ H 1 4-CF₃ 3.863 24 CH₃ H 1 3-Cl 3.72 4 25 CH₃ H 1 4-OCF₃ 4.03 3 26 CH₃ H 1 4-SCH₃ 3.723 27 I H 1 4-Br 4.00 3 28 I H 1 4-CF₃ 4.03 3 29 I H 1 3-Cl 3.86 4 30 I H1 4-OCF₃ 4.21 3 31 I H 1 4-SCH₃ 3.86 3 32 I H 1 4-F 3.55 3 33 CF₃ H 23,4-F₂ 3.55 1 34 CF₃ H 2 3-F, 4-Cl 3.76 1 35 CF₃ H 2 3-Cl, 4-F 3.81 1 36CF₃ H 2 2,4-F₂ 3.41 1 37 CF₃ H 2 3-F, 4-OCF₃ 4.08 1 38 CF₃ H 2 3-CF₃,4-Cl 4.18 1 39 CF₃ H 2 3-CF₃, 4-CH₃ 4.18 1 40 CF₃ H 2 3-CF₃, 4-OCF₃ 4.411 41 CF₃ H 2 3-CF₃, 4-F 3.90 1 42 CF₃ H 2 3-CH₃, 4-Cl 4.18 1 43 CF₃ H 23,5-Cl₂ 4.16 1 44 I H 2 3,4-Cl₂ 4.06 1 45 CF₃ H 2 2-F, 4-Cl 3.68 1 46 IH 1 4-Cl 3.74 3 47 CF₃ 5′-F 2 3,4-Cl₂ 4.11 1, 2 48 CF₃ 3′-F 2 3,4-Cl₂3.81 1, 2 49 Cl H 1 4-Cl 3.64 3 50 Br H 1 4-Cl 3.66 3Preparation of Starting Materials of the Formula (III)

Examples (III-1)

Under an atmosphere of argon, 38.8 g (223 mmol) of3-chloro-4-fluorophenylboronic acid and 40.6 g (186 mmol) of2-iodoaniline are dissolved in 220 ml of toluene, 22 ml of ethanol and45 ml of a 4 M sodium bicarbonate solution. 4.3 g (4 mmol) oftetrakis(triphenylphosphine)palladium(0) are added, and the reactionsolution is heated at 80° C. for 2–16 h. For work-up, the phases areseparated and the organic phase is dried over magnesium sulphate andconcentrated. The crude product is purified by column chromatography(cyclohexane/ethyl acetate 3:1) and/or by recrystallization.

This gives 19.8 g (48% of theory) of3′-chloro-4′-fluoro-1,1′-biphenyl-2-amine of logP (pH 2.3)=3.01.

Preparation of Starting Materials of the Formula (IV)

Example (IV-1)

7.5 g (0.044 mol) of 2-bromaniline are initially charged in 100 ml ofacetonitrile, and 7.8 g (0.057 mol) of potassium carbonate and 10.0 g(0.048 mol) of 2-trifluoro-methylbenzoyl chloride are added insuccession. The reaction solution is heated under reflux for 16 h. Forwork-up, the solution is concentrated and the residue is chromatographedon silica gel using cyclohexane/ethyl acetate.

This gives 9.75 g (65% of theory) ofN-(2-bromophenyl)-2-(trifluoro-methyl)benzamide of logP (pH 2.3)=2.99.

The logP values given in the tables and preparation examples above aredetermined in accordance with EEC Directive 79/831 Annex V.48 by HPLC(High Performance Liquid Chromatography) on a reversed-phase column(C18). Temperature: 43° C.

The determination is carried out in the acidic range at pH 2.3 using themobile phases 0.1% aqueous phosphoric acid and acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile.

Calibration is carried out using unbranched alkan-4-ones (of 3 to 16carbon atoms) with known logP values (determination of the logP valuesby the retention time using linear interpolation between two successivealkanones).

Use Examples Example A

Podosphaera test (apple)/protective Solvents: 24.5 parts by weight ofacetone 24.5 parts by weight of dimethylacetamide Emulsifier:  1.0 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of the apple mildew pathogen Podosphaera leucotricha.The plants are then placed in a greenhouse at about 23° C. and arelative atmospheric humidity of about 70%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE A Podosphaera test (apple)/protective Application rate of activecompound Efficacy Active compound in g/ha in % 7

100 100 12

100 100 1

100 100 33

100 100 34

100 100 35

100 100 4

100 100 41

100 94 42

100 100 2

100 100 3

100 99

Example B

Sphaerotheca test (cucumber)/protective Solvents: 24.5 parts by weightof acetone 24.5 parts by weight of dimethylacetamide Emulsifier:  1.0part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousspore suspension of Sphaerotheca fuliginea. The plants are then placedin a greenhouse at about 23° C. and a relative atmospheric humidity ofabout 70%.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE B Sphaerotheca test (cucumber)/protective Application rate ofactive compound Efficacy Active compound in g/ha in % 7

100 100 1

100 94 33

100 82 34

100 95 35

100 93 4

100 100 41

100 100 42

100 100 2

100 94 3

100 100

Example C

Venturia test (apple)/protective Solvents: 24.5 parts by weight ofacetone 24.5 parts by weight of dimethylacetamide Emulsifier:  1.0 partby weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are inoculated with an aqueousconidia suspension of the apple scab pathogen Venturia inaequalis andthen remain in an incubation cabin at about 20° C. and 100% relativeatmospheric humidity for 1 day.

The plants are then placed in a greenhouse at about 21° C. and arelative atmospheric humidity of about 90%.

Evaluation is carried out 10 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE C Venturia test (apple)/protective Application rate of activecompound Efficacy Active compound in g/ha in % 7

100 100 12

100 100 1

100 97 33

100 100 34

100 100 35

100 100 4

100 100 42

100 100 3

100 100

Example D

Pyrenophora teres test (barley)/protective Solvent:  25 parts by weightof N,N-dimethylacetamide Emulsifier: 0.6 part by weight of alkylarylpolyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young plants are sprayed with thepreparation of active compound at the stated application rate. After thespray coating has dried on, the plants are sprayed with a conidiasuspension of Pyrenophora teres. The plants remain in an incubationcabin at 20° C. and 100% relative atmospheric humidity for 48 hours.

The plants are then placed in a greenhouse at about 20° C. and arelative atmospheric humidity of about 80%.

Active compounds, application rates and test results are shown in thetable below.

TABLE D Pyrenophora teres test (barley)/protective Application rate ofactive Efficacy Active compound compound in g/ha in % 7

500 90 4

500 100

Example E

Alternaria test (tomato)/protective Solvent: 49 parts by weight ofN,N-dimethylformamide Emulsifier:  1 part by weight of alkylarylpolyglycol ether

To produce a suitable p reparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for protective activity, young tomato plants are sprayed withthe preparation of active compound at the stated application rate. 1 dayafter the treatment, the plants are inoculated with a spore suspensionof Alternaria solani and are then kept at 100% relative atmospherichumidity and 20° C. for 24 h. The plants are then kept at 96% relativeatmospheric humidity and a temperature of 20° C.

Evaluation is carried out 7 days after the inoculation. 0% means anefficacy which corresponds to that of the control, whereas an efficacyof 100% means that no infection is observed.

Active compounds, application rates and test results are shown in thetable below.

TABLE E Alternaria test (tomato)/protective Application rate of activeEfficacy Active compound compound in g/ha in % 5

750 94 7

750 94 10

750 92 18

750 100 33

750 94

1. A biphenylbenzamide derivative of formula (Ia)

in which R¹ represents methyl, trifluoromethyl, chlorine, bromine, oriodine, R² represents hydrogen, R³ represents halogen, cyano, nitro,C₁–C₆-alkyl, C₁–C₄-alkoxy, C₁–C₄-alkylthio, C₁–C₄-alkylsulphonyl,C₂–C₆-alkenyl, or C₃–C₆-cycloalkyl; or represents C₁–C₆-haloalkyl,C₁–C₆-haloalkoxy, C₁–C₆-haloalkylthio, or C₁–C₆-haloalkylsulphonylhaving in each case 1 to 13 halogen atoms, and n represents 2, 3, 4, or5, where the radicals R³ may be identical or different.
 2. A compositionfor controlling unwanted microorganisms comprising one or morebiphenylbenzamide derivatives of formula (Ia) according to claim 1 andone or more extenders and/or surfactants.
 3. A process for preparing acomposition for controlling unwanted microorganisms comprising mixingone or more biphenyl-benzamide derivatives of formula (Ia) according toclaim 1 with one or more extenders and/or surfactants.
 4. A method forcontrolling unwanted microorganisms comprising applying one or morebiphenylbenzamide derivatives of formula (Ia) according to claim 1 tothe microorganisms and/or their habitat, wherein the microorganisms areselected from the group consisting of Xanthomonas species, Pseudomonasspecies, Erwinia species, Erysiphe species, Sphaerotheca species,Podosphaera species, Cochliobolus species, Uromyces species, Pucciniaspecies, Tilletia species, Ustilago species, Pellicularia species,Leptosphaeria species, and Alternaria species.
 5. A method forcontrolling unwanted microorganisms according to claim 4 wherein themicroorganisms are Xanthomonas campestris pv. oryzae, Pseudomonassyringae pv. lachrymans, Erwinia amylovora, Sphaerotheca fuliginea,Podosphaera leucotricha, Cochliobolus sativus (conidia form: Drechslera,syn: Helminthosporium), Uromyces appendiculatus, Puccinia recondita,Tilletia caries, Ustilago nuda or Ustilago avenae, Pellicularia sasakii,Leptosphaeria nodorum, or Alternaria solani.